Individualized incentives to improve financing outcomes

A payment processing system is configured to provide financing to a merchant, the merchant having an account with a payment provider who operates the payment processing system to process a plurality of financial transactions between the merchant and buyers via a mobile point-of-sale (POS) terminal. The payment processing system receives repayment of the financing from the merchant by withholding a portion of funds from the plurality of financial transactions processed for the merchant by the payment processing system. The payment processing system evaluates financial transactions conducted by the merchant through the payment processing system and, based on the evaluation, provides the merchant with one or more offers defining an incentive of financing or modification of current financing arrangements in order to induce activity by the merchant. The payment processing system identifies that the merchant has performed the activity identified in the offer and implements the incentive in the offer.